| 2025 |
| Fri., Nov. 7 | vs. Grayson County | W 62-7 | 1st Round Playoffs | | Fri., Nov. 14 | vs. Greenwood | W 42-14 | 2nd Round Playoffs | | Fri., Nov. 21 | vs. Fairdale | W 41-7 | 3rd Round Playoffs | | Fri., Nov. 28 | vs. Woodford County | W 49-6 | Semi-finals Playoffs | | Sat., Dec. 6 | @ Pulaski County | W 35-7 | Championship Game |
| 2024 |
| Fri., Nov. 8 | vs. Ohio County | W 58-0 | 1st Round Playoffs | | Fri., Nov. 15 | vs. Bowling Green | L 14-27 | 2nd Round Playoffs |
| 2023 |
| Fri., Nov. 3 | vs. Ohio County | W 67-0 | 1st Round Playoffs | | Fri., Nov. 10 | vs. South Warren | W 53-22 | 2nd Round Playoffs | | Fri., Nov. 17 | @ Atherton | W 43-7 | 3rd Round Playoffs | | Mon., Nov. 27 | @ Bowling Green | L 8-38 | Semi-finals Playoffs |
| 2022 |
| Thu., Nov. 3 | vs. Christian County | W 56-14 | 1st Round Playoffs | | Fri., Nov. 11 | vs. Greenwood | W 27-21 | 2nd Round Playoffs | | Fri., Nov. 18 | vs. Fairdale | W 36-0 | 3rd Round Playoffs | | Fri., Nov. 25 | vs. Frederick Douglass | L 2-14 | Semi-finals Playoffs |
| 2021 |
| Thu., Nov. 4 | vs. Grayson County | W 42-7 | 1st Round Playoffs | | Fri., Nov. 12 | Graves County | W 43-0 | 2nd Round Playoffs | | Fri., Nov. 19 | vs. Bullitt Central | W 56-12 | 3rd Round Playoffs | | Fri., Nov. 26 | @ Frederick Douglass | L 7-35 | Semi-finals Playoffs |
| 2020 |
| Fri., Nov. 20 | vs. Breckinridge County | W 81-6 | 1st Round Playoffs | | Fri., Nov. 27 | vs. Graves County | W 28-21 | 2nd Round Playoffs | | Fri., Dec. 4 | Fairdale | #Won 1-0 | 3rd Round Playoffs | | Fri., Dec. 11 | vs. Frederick Douglass | W 28-27 | Semi-finals Playoffs | | Sat., Dec. 19 | vs. Bowling Green | L 7-17 | Championship Game |
| 2019 |
| | Muhlenberg | W 40-0 | 1st Round Playoffs | | | Graves County | W 43-0 | 2nd Round Playoffs | | | Fairdale | W 41-6 | 3rd Round Playoffs | | | Frederick Douglass | L 17-28 | Semi-finals Playoffs |
| 2018 |
| | Greenwood | W 47-14 | 1st Round Playoffs | | | Bowling Green | W 28-21 | 2nd Round Playoffs | | | South Warren | L 7-44 | 3rd Round Playoffs |
| 2017 |
| | Bowling Green | L 14-48 | 1st Round Playoffs |
| 2016 |
| | Grayson County | W 64-14 | 1st Round Playoffs | | | Greenwood | W 28-17 | 2nd Round Playoffs | | | Bowling Green | L 21-50 | 3rd Round Playoffs |
| 2015 |
| | Grayson County | W 69-0 | 1st Round Playoffs | | | Greenwood | W 50-14 | 2nd Round Playoffs | | | Bowling Green | L 12-41 | 3rd Round Playoffs |
| 2014 |
| | Breckinridge County | W 49-0 | 1st Round Playoffs | | | Warren East | W 35-13 | 2nd Round Playoffs | | | Madisonville | W 29-28 | 3rd Round Playoffs | | | North Oldham | W 27-24 | Semi-finals Playoffs | | | Highlands | L 42-49 | Championship Game |
| 2013 |
| | Breckinridge County | W 48-6 | 1st Round Playoffs | | | Warren East | W 54-19 | 2nd Round Playoffs | | | Franklin-Simpson | W 21-13 | 3rd Round Playoffs | | | Collins | L 14-50 | Semi-finals Playoffs |
| 2012 |
| | Breckinridge County | W 56-0 | 1st Round Playoffs | | | Madisonville | W 31-7 | 2nd Round Playoffs | | | Warren East | L 7-14 | 3rd Round Playoffs |
| 2011 |
| | Warren East | W 39-14 | 1st Round Playoffs | | | Lone Oak | L 19-56 | 2nd Round Playoffs |
| 2010 |
| | Grayson County | L 22-28 | 1st Round Playoffs |
| 2009 |
| | Grayson County | W 49-21 | 1st Round Playoffs | | | Bowling Green | L 21-25 | 2nd Round Playoffs |
| 2008 |
| | Warren Central | W 22-14 | 1st Round Playoffs | | | Bowling Green | W 28-21 | 2nd Round Playoffs | | | Christian County | L 0-16 | 3rd Round Playoffs |
| 2007 |
| | Ohio County | W 49-7 | 1st Round Playoffs | | | Christian County | W 35-19 | 2nd Round Playoffs | | | Oldham County | W 14-19 | 3rd Round Playoffs | | | Bowling Green | L 13-35 | Semi-finals Playoffs |
| 2006 |
| | Grayson County | W 42-6 | 1st Round Playoffs | | | Henderson County | L 12-20 | 2nd Round Playoffs |
| 2005 |
| | Graves County | L 0-14 | 1st Round Playoffs |
| 2003 |
| | Christian County | L 18-39 | 1st Round Playoffs |
| 2002 |
| | Henderson | L 7-49 | 1st Round Playoffs |
| 2001 |
| | Graves County | W 20-18 | 1st Round Playoffs | | | Ohio County | W 55-0 | 2nd Round Playoffs | | | Apollo | W 49-14 | 3rd Round Playoffs | | | Male | L 6-23 | Semi-finals Playoffs |
| 2000 |
| | Union County | W 44-6 | 1st Round Playoffs | | | Paducah Tilghman | W 35-28 | 2nd Round Playoffs | | | Bowling Green | W 28-0 | 3rd Round Playoffs | | | Waggener | W 56-22 | Semi-finals Playoffs | | | Highlands | L 27-48 | Championship Game |
| 1999 |
| | Hopkins County Central | W 14-7 | 1st Round Playoffs | | | Warren Central | W 21-0 | 2nd Round Playoffs | | | Franklin-Simpson | W 16-15 | 3rd Round Playoffs | | | Bullitt East | W 21-6 | Semi-finals Playoffs | | | Highlands | L 10-48 | Championship Game |
| 1998 |
| | Hopkinsville | W 35-13 | 1st Round Playoffs | | | Paducah Tilghman | W 23-20 | 2nd Round Playoffs | | | Bowling Green | L 7-14 | 3rd Round Playoffs |
| 1997 |
| | Hopkinsville | W 1-0 | 1st Round Playoffs |
| 1996 |
| | Calloway County | L 21-55 | 1st Round Playoffs |
| 1995 |
| | Calloway County | L 7-38 | 1st Round Playoffs |
| 1994 |
| | Hopkinsville | L 17-27 | 1st Round Playoffs |
| 1993 |
| | Calloway County | W 42-34 | 1st Round Playoffs | | | Bowling Green | L 12-20 | 2nd Round Playoffs |
| 1992 |
| | Hopkinsville | W 21-18 | 1st Round Playoffs | | | Bowling Green | L 20-21 | 2nd Round Playoffs |
| 1991 |
| | Hopkinsville | W 17-0 | 1st Round Playoffs | | | Paducah Tilghman | L 7-40 | 2nd Round Playoffs |
| 1990 |
| | Bullitt Central | W 31-7 | 1st Round Playoffs | | | Paducah Tilghman | W 14-12 | 2nd Round Playoffs | | | Bowling Green | W 10-0 | 3rd Round Playoffs | | | Lincoln County | L 3-27 | Semi-finals Playoffs |
| 1989 |
| | Bullitt Central | W 21-7 | 1st Round Playoffs | | | Paducah Tilghman | L 7-27 | 2nd Round Playoffs |
| 1988 |
| | Paducah Tilghman | L 20-40 | 1st Round Playoffs |
| 1986 |
| | Ohio County | W 35-0 | 1st Round Playoffs | | | Paducah Tilghman | W 10-7 | 2nd Round Playoffs | | | Montgomery County | W 29-16 | Semi-finals Playoffs | | | Belfry | W 14-0 | Championship Game |
| 1985 |
| | Shelby County | W 14-7 | 1st Round Playoffs | | | Lexington Lafayette | L 13-14 | 2nd Round Playoffs |
| 1983 |
| | Madisonville | W 6-3 | 1st Round Playoffs | | | North Hardin | W 28-21 | 2nd Round Playoffs | | | Boone County | W 34-17 | Semi-finals Playoffs | | | Trinity | L 7-26 | Championship Game |
| 1982 |
| | Christian County | L 7-35 | 1st Round Playoffs |
| 1981 |
| | Owensboro Catholic | W 28-18 | 1st Round Playoffs |
| 1980 |
| | Paducah Tilghman | L 14-40 | 1st Round Playoffs |
| 1979 |
| | Bowling Green | W 34-14 | 1st Round Playoffs | | | Franklin County | W 26-6 | 2nd Round Playoffs | | | Henry Clay | L 6-14 | Semi-finals Playoffs |
| 1978 |
| | Owensboro Catholic | W 21-0 | 1st Round Playoffs |
| 1976 |
| | Franklin-Simpson | W 42-7 | 1st Round Playoffs |
| 1975 |
| | Paducah Tilghman | L 17-23 | 1st Round Playoffs |
| 1974 |
| | Mayfield | W 28-13 | 1st Round Playoffs | | | Somerset | W 32-0 | Semi-finals Playoffs | | | Middlesboro | W 17-14 | Championship Game |
| 1973 |
| | Henderson City | W 51-6 | 1st Round Playoffs |
| 1972 |
| | Henderson City | W 33-6 | 1st Round Playoffs |
| 1971 |
| | Union County | L 6-9 | 1st Round Playoffs |
| 1970 |
| | Henderson | W 21-0 | 1st Round Playoffs |
|
| Owensboro Playoff Totals |
| Record |
85-42-0 3481-2203 |
| Home Record | 15-3 |
| Away Record | 2-2 |
|
